トリメトレキサート、トリメトレキセート
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/05/20 00:50:27」(JST)
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Trimetrexate
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| Systematic (IUPAC) name |
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5-methyl-6-[(3,4,5-trimethoxyphenyl) aminomethyl] quinazoline-2,4-diamine
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| Clinical data |
| AHFS/Drugs.com |
Consumer Drug Information |
| MedlinePlus |
a694019 |
| Pharmacokinetic data |
| Bioavailability |
VD: 20-30 Liters |
| Metabolism |
Oxidative O-demethylation, followed by conjugation with glucuronide or sulfate |
| Biological half-life |
11 to 12 hours |
| Identifiers |
| CAS Number |
52128-35-5 Y |
| ATC code |
P01AX07 (WHO) |
| PubChem |
CID 5583 |
| IUPHAR/BPS |
7613 |
| DrugBank |
DB01157 Y |
| ChemSpider |
5381 Y |
| UNII |
UPN4ITI8T4 Y |
| KEGG |
D06238 Y |
| ChEMBL |
CHEMBL119 Y |
| Chemical data |
| Formula |
C19H23N5O3 |
| Molar mass |
369.418 g/mol |
SMILES
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n3c1c(c(c(cc1)CNc2cc(OC)c(OC)c(OC)c2)C)c(nc3N)N
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InChI
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InChI=1S/C19H23N5O3/c1-10-11(5-6-13-16(10)18(20)24-19(21)23-13)9-22-12-7-14(25-2)17(27-4)15(8-12)26-3/h5-8,22H,9H2,1-4H3,(H4,20,21,23,24) Y
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Key:NOYPYLRCIDNJJB-UHFFFAOYSA-N Y
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| (verify) |
Trimetrexate is a quinazoline derivative. It is a dihydrofolate reductase inhibitor.[1]
Uses
It has been used with leucovorin in treating pneumocystis pneumonia.[2]
It has been investigated for use in treating leiomyosarcoma.[3] It is a methotrexate (MTX) analog that is active against transport-deficient MTX-resistant tumor cells that overcome the acquired and natural resistance to methotrexate. Other uses include skin lymphoma. [4]
References
- ^ Wong BK, Woolf TF, Chang T, Whitfield LR (1990). "Metabolic disposition of trimetrexate, a nonclassical dihydrofolate reductase inhibitor, in rat and dog". Drug Metab. Dispos. 18 (6): 980–6. PMID 1981548.
- ^ Sattler FR, Allegra CJ, Verdegem TD, et al. (January 1990). "Trimetrexate-leucovorin dosage evaluation study for treatment of Pneumocystis carinii pneumonia". J. Infect. Dis. 161 (1): 91–6. doi:10.1093/infdis/161.1.91. PMID 2136905.
- ^ Smith HO, Blessing JA, Vaccarello L (January 2002). "Trimetrexate in the treatment of recurrent or advanced leiomyosarcoma of the uterus: a phase II study of the Gynecologic Oncology Group". Gynecol. Oncol. 84 (1): 140–4. doi:10.1006/gyno.2001.6482. PMID 11748990.
- ^ Trimetrexate in relapsed T-cell lymphoma with skin involvement. J Clin Oncol. 2002 Jun 15;20(12):2876-80.
External links
- MedlinePlus DrugInfo uspdi-202693
- DDB 30480
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Antiparasitics – antiprotozoal agents – Chromalveolate antiparasitics (P01)
|
|
Alveo-
late |
Apicom-
plexa |
Conoidasida/
(Coccidiostats) |
| Cryptosporidiosis |
- thiazolide (nitazoxanide)
|
|
| Isosporiasis |
- trimethoprim/sulfamethoxazole#
|
|
| Toxoplasmosis |
- pyrimethamine
- sulfadiazine
|
|
|
| Aconoidasida |
| Malaria |
Individual
agents |
Hemozoin
inhibitors |
| aminoquinolines |
- (4-): amodiaquine#
- chloroquine#
- Tafenoquine
- (8-): primaquine#
- pamaquine
|
|
| 4-methanolquinolines |
- mefloquine#
- quinine#
- quinidine
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|
| Other |
|
|
|
| Antifolates |
DHFR inhibitors
(antifols) |
- proguanil#
- chlorproguanil
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|
| Sulfonamides |
- sulfadoxine
- sulfamethoxypyrazine
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|
| Coformulation |
- sulfadoxine/pyrimethamine (SP)#
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|
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Sesquiterpene
lactones |
- artemether#
- artesunate#
- dihydroartemisinin
- artemotil
- artemisinin
|
|
| Other |
- atovaquone (with proguanil as Malarone)
- tetracycline
- doxycycline#
- clindamycin
- pyronaridine
- piperaquine
|
|
|
Combi-
nations |
| Fixed-dose (coformulated) ACTs |
- artemether/lumefantrine#
- artesunate/amodiaquine (ASAQ)
- artesunate/mefloquine (ASMQ)
- dihydroartemisinin/piperaquine
- artesunate/pyronaridine
- arterolane/piperaquine
|
|
Other combinations
(not co-formulated) |
- artesunate/SP
- artesunate/mefloquine
- quinine/tetracycline
- quinine/doxycycline
- quinine/clindamycin
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|
|
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| Babesiosis |
|
|
|
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Cilio-
phora |
- Balantidiasis: Tetracycline
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|
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Hetero-
kont |
- Blastocystosis: Metronidazole
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|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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|
UpToDate Contents
全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.
English Journal
- New small-molecule inhibitors of dihydrofolate reductase inhibit Streptococcus mutans.
- Zhang Q1, Nguyen T2, McMichael M2, Velu SE2, Zou J3, Zhou X3, Wu H4.
- International journal of antimicrobial agents.Int J Antimicrob Agents.2015 Aug;46(2):174-82. doi: 10.1016/j.ijantimicag.2015.03.015. Epub 2015 May 8.
- Streptococcus mutans is a major aetiological agent of dental caries. Formation of biofilms is a key virulence factor of S. mutans. Drugs that inhibit S. mutans biofilms may have therapeutic potential. Dihydrofolate reductase (DHFR) plays a critical role in regulating the metabolism of folate. DHFR i
- PMID 26022931
- Methotrexate analogues display enhanced inhibition of TNF-α production in whole blood from RA patients.
- van der Heijden JW1, Assaraf YG, Gerards AH, Oerlemans R, Lems WF, Scheper RJ, Dijkmans BA, Jansen G.
- Scandinavian journal of rheumatology.Scand J Rheumatol.2014;43(1):9-16. doi: 10.3109/03009742.2013.797490. Epub 2013 Aug 30.
- OBJECTIVES: Although methotrexate (MTX) is the anchor drug in the treatment of rheumatoid arthritis (RA), patients experience clinical resistance to MTX upon prolonged treatment. We explored whether new-generation antifolates elicit superior anti-inflammatory properties when compared to MTX, based o
- PMID 23987246
- Identification of repurposed small molecule drugs for chordoma therapy.
- Xia M1, Huang R, Sakamuru S, Alcorta D, Cho MH, Lee DH, Park DM, Kelley MJ, Sommer J, Austin CP.
- Cancer biology & therapy.Cancer Biol Ther.2013 Jul;14(7):638-47. doi: 10.4161/cbt.24596. Epub 2013 May 10.
- Chordoma is a rare, slow growing malignant tumor arising from remnants of the fetal notochord. Surgery is the first choice for chordoma treatment, followed by radiotherapy, although postoperative complications remain significant. Recurrence of the disease occurs frequently due to the anatomy of the
- PMID 23792643
Japanese Journal
- Microsatellite instability and clonal heterogeneity of MDR1 messenger RNA expression in trimetrexate-resistant human leukemia MOLT-3 cells developed in thymidine
- Cytotoxicity of Trimetrexate against Antifolate-resistant Human T-Cell Leukemia Cell Lines Developed in Oxidized or Reduced Folate
- Japanese journal of cancer research : gann 88(9), 900-906, 1997-09-30
- NAID 10008080894
- Growth inhibitory effects of antifolates against an adriamycin-resistant human small cell lung cancer cell line
Related Links
- trimetrexate tri·me·trex·ate (trī'mĭ-trěk'sāt') n. An antineoplastic agent and antiprotozoal orphan drug used in the treatment of Pneumocystis carinii pneumonia in AIDS patients.
- Synopsis Trimetrexate is a folinic acid analogue structurally related to methotrexate, whose primary mechanism of action is believed to be inhibition of dihydrofolate reductase. This r ... Various sections of the manuscript reviewed by: C.J. Allegra ...
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